1. Field of the Invention
This invention relates to new alkyl-substituted bicycloalkyl ether compositions, and particularly to monoalkyl ethers of alkyl-substituted bicyclo (2.2.1) heptanols, which are useful in the preparation of valuable lubricant compositions, and to an efficient process for preparing the new ethers in high yields from alkyl-substituted norbornene compounds.
The invention specifically provides new and particularly useful monoalkyl ethers of alkyl-substituted bicyclo (2.2.1) heptanols which can be generically represented by the formula ##STR1## wherein R is hydrogen or methyl, x is an integer ranging from 4 to 18, y and z are integers ranging from 0 to 16 whose sum must be 8-16, and the sum of x+y+z must be 20 to 36. The invention also provides an efficient process for preparing the new ethers which comprises reacting an alkyl-substituted norbornene with a monohydric alcohol in the presence of an acidic catalyst.
The new ethers of the invention possess valuable properties which make them suitable for use in important commercial applications, such as in the preparation of lubricant compositions. Because of their high boiling points, good stability and desired viscosity and lubricating properties the new ethers of this invention are particularly useful in the preparation of improved lubricant compositions.
2. Prior Art
Some ethers of bicyclo (2.2.1) heptanol have been prepared in the past, such as described in U.S. Pat. No. 3,370,080, by hydrating norbornene to form norbornane alcohol and reacting that secondary alcohol with an alkylene oxide. Such products have a polyoxyalkylene group which limits the oleophilic properties of the ethers. The oleophilic properties of the products of U.S. Pat. No. 3,370,080 are further restricted by the limitation on the size of the alkyl side chains as noted in that reference.
Further advantage of the present ether compositions over other types of known synthetic lubricant compositions, and particularly those of the ester type, include the improved resistance to alkali and hydrolysis of the ether linkage over the ester linkages of the known compounds. Additional advantage is also found in the fact that the new ether compositions can be prepared from inexpensive compounds, such as alphaolefins and cyclic diolefins, and obtained in high yield by a simple two-step process; thus presenting an economic advantage over many of the known synthetic lubricant compositions.